When I play GSC the hardest one depends on the starter. If I pick Chikorita, Bugsy's Scyther is the hardest. If I pick Cyndaquil, Whitney's Miltank is the hardest. If I pick Totodile, Clair's Kingdra is the hardest.

On Route 47 in HG/SS, you come across a trainer team, Double Team Thom and Kae, with Electabuzz and Magmar, around the same level as most teams at that point, maybe a bit lower. This would be fine if they didn't have Thunderbolt and Flamethrower to tear things apart... Actually, Magmar also has Confuse Ray and Protect while Electabuzz has Thunder Wave and Light Screen so it's a really annoying battle.

I've never understood why people have so much trouble with Whitney's Miltank. I just destroy her with Geodude every time.

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I don't understand either. I had my Dunsparce rage its way past her.

When I first battled Brock in Yellow, his team, especially Onix, was incredibly difficult for me to beat. I was a beginner, so I trained Pidgeotto to ridiculous levels to beat him. I guess Misty in Yellow and Cynthia in DPPt were more of a challenge for me, though. Starmie and Garchomp frustrated me to no limit as they repeatedly shrugged off weak damage and minced my entire team.

Oh, man, Cynthia takes the cake for me. Her freakin' Garchomp kills everything, and I never seem to be adequately prepared for it.
I've never had too much trouble with Misty except for maybe my first time playing when I had an overleveled Charmeleon and a Bellsprout I was too lazy to train. Other than that, though, I've always managed to beat her fairly easily. I will agree that Whitney's Miltank is really annoying, especially if you've never fought it before. The second and third times around though you wise up and get a Geodude or Heracross or something.

When I first battled Brock in Yellow, his team, especially Onix, was incredibly difficult for me to beat. I was a beginner, so I trained Pidgeotto to ridiculous levels to beat him. I guess Misty in Yellow and Cynthia in DPPt were more of a challenge for me, though. Starmie and Garchomp frustrated me to no limit as they repeatedly shrugged off weak damage and minced my entire team.

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I was going to post Brock in Yellow too. Too difficult for beginners, what to do against rock types without any grass or water mon available at that point?
At least against Misty is intuitive the use of grass mons. I can't understand why nobody but you has mentioned him yet.

Personally I don't find Lenora difficult without the use of Fighters/Roggenrola barring Hypnosis hits from Watchog.

I agree with Norman, Blanca, and DD+EQ Altaria from Winona. Wattson is pretty annoying with Thunder Wave+Supersonic and its Magnemite/ton with 542524 resistances.

Speaking of double battles, Clair/Lance in HGSS Dragon's Den if you picked Chikorita. Your rival is lucky to last 3 turns, and Typhlosion will always die 1st turn. I ended up using a parafusion combo with Ampharos (Signal Beam is useful, wut?) to get past those two, because you will be on your own for the majority of the battle.

Oh dear God, how the HELL did we forget BW Cynthia? You're exploring a beach town, breathing a sigh of relief at not having to encounter any Trainers in the city, maybe you've defeated the Rich family or are getting ready to explore the underwater ruins. You go into the villa, seeing if there are any interesting characters, and suddenly...

Oddly enough I never had a lot of trouble with Whitney, I have no painful memories anyway. Misty is definitely up there and so was Red in GSC, I have a very vivid memory of beating Red with my Venusaur from Yellow version xD

The one that really sticks out for me though was BW Ghetsis, specifically Hydreigon. I remember thinking, well thats it I've got nothing to take it down, had to use so many revives. I think it sticks out more because now that I'm older I recognize when I'm frustrated more. When I was younger I think I just kinda lost and went aw, trained, and then did it again and again. Now I'm older I get frustrated because I probably think I shouldn't be losing.

Doubles President

Yellow Brock doesn't have a single Rock move, and Butterfree pretty much wipes the floor with him. Mankey works too.

In DPPt, the Raichu-Gyarados double battle on Route 210 is pretty damn hard. Raichu paralyzes you and Gyarados cleans up your now much slower team. Not to mention they do a nice job at covering each other's weaknesses on their own...

He caught me completely unawares and nearly killed my team since I hadn't restocked on healing items in a while. Made escaping the cave a bit more difficult, too; I continued to stumble into some of the other (not quite as tough) trainers and things were getting messy.

He caught me completely unawares and nearly killed my team since I hadn't restocked on healing items in a while. Made escaping the cave a bit more difficult, too; I continued to stumble into some of the other (not quite as tough) trainers and things were getting messy.

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That happened to me too. My White team was not even level 50 when I ran into this guy. Had to use that blasted Level 70 Volcarona to finish him!

For a Pikachu solo run of Yellow, Brock isn't too hard if you grind for Double Team. That combined with Tail Whip and Quick Attack make that fight easier, especially since Brock has no Rock- or Ground-type attacks on him. Misty is roughly equally tough; the only way to make her easy is to outspeed her Starmie, as otherwise Bubblebeam would hurt.

He caught me completely unawares and nearly killed my team since I hadn't restocked on healing items in a while. Made escaping the cave a bit more difficult, too; I continued to stumble into some of the other (not quite as tough) trainers and things were getting messy.

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YES YES! I was going to mention this guy too! In my hard Black Scramble he literally took out my entire team except for my HM slave, and I had to spam revives to win. And my team outleveled him. To be fair, I am using an odd mixture of mons that are either incredibly slow or incredibly frail, and most of them have crippling restrictions. But still!

Some other honourable BW post-game mentions go to:
Ace Trainer Junko: (Route 14, lv 68 Purgly, Espeon and Lapras). At the very end of an already crowded route, with Pokemon that are SURE to outlevel yours unless you've ground like crazy. Even Purgly is a sonova bitch; it has Attract. Espeon is just fast and powerful and will eat you alive without a resist, wheras Lapras is super bulky and has Dragon Dance. KO'd over half my team, though again, it should be noted my team isn't exactly ideal.
Ace Trainer Kip: (Route 14, lv 68 Absol, Dodrio and Walrien). Same deal as Junko, though not quite as bad. Still outlevels the shit out of you and his Pokemon are good enough to fuck you up.

A lot of the trainers post game also have OHKO moves, and since you're likely to be outleveled you'll find yourself actually falling victim to them.

I'll be putting up the chapter of my scramble where all this shit happens and you can read it for yourself, but seriously the eastern half on Unova is not for the unprepared.

The only way I reliably beat Lenora is by sending in a sacrifice against Watchog's first Retaliate, otherwise, it WILL take out a key player in the fight. Also I refuse to use Roggenrola because fuck that guy.

I was playing through Emerald again, and I'd forgotten just how dangerous Wallace's Gyarados is. Surf/Earthquake/Hyper Beam/Dragon Dance isn't fun. Gyarados's bulk is more than enough to survive a hit or two, giving it time to set up a couple of DDs. From there it can wipe your team with Hyper Beam or Earthquake, and it pretty much OHKOs everything by that stage. You can't even revenge kill it because DD boosts speed too. Your only real way to beat it is by sacking something and taking advantage of the free turn, but if you do what I stupidly did and get your Electric type KOd beforehand, then it sure isn't going to be easy.

Aarons Vespiquen, Oh god right when i destroy his Scizor with my level 48 Infernape he sends out vespiquen who immediatly spams defend and heal order while i try to kill it with Fire Blast, it took 20 turns to kill it and only because i got a critical hit and a lot of Ethers

Aarons Vespiquen, Oh god right when i destroy his Scizor with my level 48 Infernape he sends out vespiquen who immediatly spams defend and heal order while i try to kill it with Fire Blast, it took 20 turns to kill it and only because i got a critical hit and a lot of Ethers

For me I would it is Cyrus's team in Platinum. I think its mainly difficult if you have a certain team. I chose pliplup and Empolean was useless against his team,most notably Gyrados. I think it would have been easier if I had stuff to combat his team. Especially since all his team is either part dark or flying. Finally was able to win by doing revive abuse.

Orange Islands

Those were hard, 5 matches in a row and Espeon basically destroys half your team if you aren't super prepared for it. Totally agree with all the other trainers people are posting. Though there is one guy in BW with a Bouncing Mantine that gave my friends a lot of trouble...